2-Methyl-3-phenylnaphthoquinone

Base Information

• Chemical Name: 2-Methyl-3-phenylnaphthoquinone
• CAS No.: 18690-79-4
• Molecular Formula: C17H12O2
• Molecular Weight: 248.281
• DSSTox Substance ID: DTXSID90434219
• Nikkaji Number: J514.064A
• Wikidata: Q82248567
• Mol file: 18690-79-4.mol

Synonyms:2-methyl-3-phenylnaphthoquinone;2-methyl-3-phenylnaphthalene-1,4-dione;18690-79-4;2-Methyl-3-phenyl-1,4-naphthoquinone;SCHEMBL9695242;DTXSID90434219;GMOSYCUDTZFACG-UHFFFAOYSA-N

Chemical Property of 2-Methyl-3-phenylnaphthoquinone

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 248.083729621
• Heavy Atom Count: 19
• Complexity: 427

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)C3=CC=CC=C3

Technology Process of 2-Methyl-3-phenylnaphthoquinone

There total 15 articles about 2-Methyl-3-phenylnaphthoquinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

2-phenyl[1,4]naphthoquinone (2348-77-8) + tert-butyl alcohol (75-65-0) → 2-methyl-3-phenylnaphthalene-1,4-dione (18690-79-4)

Guidance literature:

With iron(III)-acetylacetonate; bis-[(trifluoroacetoxy)iodo]benzene; at 120 ℃; for 5h; Sealed tube; Green chemistry;

DOI:10.1055/s-0039-1690193

Reference yield: 89.0%

1-[2-(2-phenylethynyl)phenyl]propan-1-one → 2-methyl-3-phenylnaphthalene-1,4-dione (18690-79-4)

Guidance literature:

With copper(l) iodide; copper(II) bis(trifluoromethanesulfonate); dimethyl sulfoxide; at 140 ℃; for 6h;

Reference yield: 86.0%

1-Phenylprop-1-yne (673-32-5) → 2-methyl-3-phenylnaphthalene-1,4-dione (18690-79-4)

Guidance literature:

1-Phenylprop-1-yne; Ph-C(OMe)=Cr(CO)5; In tetrahydrofuran; at 130 ℃; for 0.0833333h; microwave irradiation;

With ammonium cerium(IV) nitrate; In tetrahydrofuran; for 0.333333h; Further stages.;

DOI:10.1039/b206981b

upstream raw materials:

4-Hydroxy-2-methyl-3,4-diphenyl-cyclobut-2-enone

1-Phenylprop-1-yne

benzocyclobutene-1,2-dione

menadione

Refernces

• 1、 Orihara, Tatsuya,Kawaguchi, Masaki,Hosoya, Keisuke,Tsutsumi, Ryosuke,Yamanaka, Masahiro,Odagi, Minami,Nagasawa, Kazuo. "Enantioselective Epoxidation of 2,3-Disubstituted Naphthoquinones by a Side Chain Truncated Guanidine-Urea Bifunctional Organocatalyst". . p. 15232 - 15240. Retrieved 2020.
• 2、 Zhou, Bingwei,Liu, Qian,Wang, Heng,Jin, Hongwei,Liu, Yunkui. "CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones: Efficient synthesis of 1,4-naphthoquinones". . p. 3815 - 3821. Retrieved 2019/06/14.
• 3、 Sato, Naoko,Li, Wei,Takemoto, Hiroaki,Takeuchi, Mio,Nakamura, Ai,Tokura, Emi,Akahane, Chie,Ueno, Kanako,Komatsu, Kana,Kuriyama, Noriko,Onoda, Toshihisa,Higai, Koji,Koike, Kazuo. "Comprehensive evaluation of antioxidant effects of Japanese Kampo medicines led to identification of Tsudosan formulation as a potent antioxidant agent". . p. 163 - 172. Retrieved 2018/11/06.